5-Fluoro-2-(hydroxymethyl)benzoic acid → 5-Fluoro-2-formylbenzoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][OH:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>O1CCCC1.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 5-fluoro-2-(hydroxymethyl)benzoic acid (0.518 g, 3.04 mmol) and manganese(IV) oxide (3.71 g, 42.6 mmol) in tetrahydrofuran (25 mL) was stirred at room temperature for 16 hr. The insoluble material was removed by filtration through CELITE®. The filtrate was concentrated under vacuum to dryness. The residue was dissolved in CH2Cl2 (100 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.211 g, 1.255 mmol, 41.2% yield) as a white solid.
Workup
- customThe insoluble material was removed by filtration through CELITE®
- concentrationThe filtrate was concentrated under vacuum to dryness
- dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
- dry with materialdried over anhydrous MgSO4
- customRemoval of solvent under vacuum
Sources & evidence
- ORD record
- ord-73088f2ae7fb4ad3b9414e44c0a9ef94
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
Loading…